


Drabble Request Collection- Pennywise (1990)

by red_and_blue_sewer_circus



Series: Drabble collections [2]
Category: IT (1990), IT - Stephen King
Genre: Anal Sex, BDSM, Breeding, Butt Plugs, Cigars, Cock Warming, Cock Worship, Collars, Daddy Kink, Dirty Talk, Double Penetration, F/M, Fingerfucking, Forced Orgasm, Glove Kink, Human/Monster Romance, Humiliation, Knotting, Maledom, Master/Pet, Mind Break, Oral Fixation, Oral Knotting, Oral Sex, Orgasm Delay/Denial, Orgasm Denial, Pet Names, Praise Kink, Rough Oral Sex, Spanking, Whipping, thigh fucking, thigh grinding
Language: English
Status: In-Progress
Published: 2019-07-24
Updated: 2019-10-04
Packaged: 2020-07-12 13:04:02
Rating: Explicit
Warnings: Graphic Depictions Of Violence
Chapters: 21
Words: 9,325
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/19946629
Author URL: https://archiveofourown.org/users/red_and_blue_sewer_circus/pseuds/red_and_blue_sewer_circus
Summary: A collection of drabbles requested by users on tumblr. They vary from explicit smut, to horror, to sometimes a little bit of humor or fluff. Pennywise (2017) and Rufo coming soon!Most will be reader x but a few are third person POV





	1. Chapter 1

**Author's Note:**

> The prompt that was requested will be posted under the notes for each chapter.

**Notes for the Chapter:**

> "Harder! Harder!"

“Oh fuck! Yes! Papa!” 

You threw your head back and moaned as the clown ran his tongue over your breasts. Yellowed teeth bit down on your nipple and pulled, stretching your skin before he released it.

"That's it bayybe-dolll. Ride this fucking cock."

He reclined back in his chair and smiled up at you as he watched your tits bounce. Lipstick was smeared around his mouth and over your breasts but you didn’t dare stop.

“Yes Papa.. your cock is so fucking good!”

Long, green claws ripped through his gloves and scratched your skin as he reached around to cup your ass. He laughed as he pulled you down faster, making you bounce harder.

“That’s it girl. Harder! Harder!”


	2. Chapter 2

**Notes for the Chapter:**

> "Oh look at you. All tied up and ready to be fucked."

You lay in your bed, tossing and turning, unable to go to sleep. Thoughts of a certain red haired clown fill your mind making you restless and needy.

“Papa…” 

You groan into your pillow before rolling onto your back and reaching a hand down to your soaked panties. You knew he wasn’t human, that he was dangerous, but seeing him around town had sent a thrill through your body.

You had been on your way home from work when he finally appeared in front of you.

“I can smell it on you ya know. Been a while since I had a little fun with a human woman.”

He laughed as you stared at him in fascination.

“Who.. are you?”

“Me? I’m many things girly. I can be your worst nightmare, or in your case, your greatest pleasure.” 

Confusion must have been written across your face because he winked at you.

“Call me Papa”

A dog barking down the street had drawn your attention away from him and when you turned back, he was gone. Your body was flushed and you were hardly able to walk as you made it home and got ready for bed. You told yourself you would just rub one out then you would finally be able to sleep. Just a little something to relieve the pressure.

You moan and arch your back, spreading your legs a little wider as your fingers brush over your clit. 

“Mm.. Papa..”

You freeze as you smell smoke. Was something on fire? No, this smells like.. cigar smoke? You scream as streams of colorful scarves come up from under your bed and tie your arms and legs down. You thrash and pull, but it's no use. You're stuck.

The door to your closet creaks open and there he stands, his clown makeup lit by the cigar between his lips. He inhales he steps into the bedroom. Lifting his gloved hand, he pulls the cigar from his lips and exhales a large cloud of smoke as his eyes roam over your body.

“Well.. what have we here?” 

He uses his free hand to tug the scarves and make sure they are secure before running a hand up your thigh and tracing over your wet panties.

“Oh, look at you! All tied up and ready to be fucked!”

He smiles and flicks his cigar away.

“Better not let it go to waste”


	3. Chapter 3

**Notes for the Chapter:**

> “I’m not done yet! Spread your legs and lie the fuck still until I tell you to move!”

“That’s it baby doll, swallow it all down like a good girl.”

The clown held your head down on his cock by the back of your head as he came down your throat. You swallowed several mouthfuls of his seed before he finally pulled back and let you lick him clean.

His cock appeared almost human, except for the bright red tip which showed in stark contrast against the pale white flesh. That, and the slight bulge in his already impressive girth halfway down his length. You knew he could change its form at will, but he also knew it rubbed against your sweet spot when he was going deep. He knew just how to tease the inside your pussy with it if he was feeling especially cruel.

He chuckled as he watched you. His eyes glowed a faint silver as you swirled your tongue around his knot.

“You know sweet tits, you make a compelling argument for women in this day and age of being my favorite. You’re not afraid to swallow a load that’s for sure.”

You finished cleaning him and returned his smile as you stood.

“Thank you Papa, but I have to run, I’m late for work.”

The smile fell from his face and he bounced up from the edge of your bed.

“I tell you when I’m done with you and I’m not done yet!”

His gloved hand covered your face and pushed your head back until you fell on the bed. He glared down at you and sneered as he reached down to stroke his cock.

“Now, spread your legs and lie the fuck still until I tell you to move!”


	4. Chapter 4

**Notes for the Chapter:**

> “Who the fuck do you think you’re talking to?”

“Papa! Please.. I need it.”

You whined as the old clown reclined in his chair and ignored your desperate pleas. You stood before him, dressed in his favorite lingerie and he couldn’t even be bothered to put down his cigar.

“I told ya kid, didn’t I? I said if you didn’t behave like a good girl you wouldn’t be gettin any lovin from Papa for a week. I mean’t what I said, little brat.” 

He took a deep drag of his cigar and exhaled a huge cloud of smoke in your direction. His eyes burned into yours until finally, with a stamp of your foot, you turned around to leave.

“Fine! I’ll just go find someone who will play with me. Someone younger, who can keep up with my nee….” 

Your voice was choked off as a gloved hand tightened around your throat and lifted you into the air. The old clown had suddenly appeared before you, yellow and red eyes blazing as he bared razor sharp teeth inches from your face.

“Who the fuck do you think you are talking to? Little bitch. I am eternal. The eater of worlds, and you?” 

He dropped you to the ground.

“You are nothing to me. Entertainment. Something to break up the monotony of being on this pathetic rock.”

He grabbed you by the hair and shoved your face against the front of his costume. You felt his cock squirm against your cheek. 

“I am a god and you are a toy to keep my cock warm. Understand?”


	5. Chapter 5

**Notes for the Chapter:**

> “Let’s make a fucking baby"

A knock from the inside of your closet woke you from a deep sleep and you yawned as you got up from your bed. Rubbing the sleep from your eyes, you made your way to the closet door and weren’t really that surprised when multicolored balloons flooded into your bedroom.

The old clown stepped into your room with one exaggerated step and beamed at you as he stuffed a bouquet of flowers and a tray of chocolates into your arms. 

“Papa” you smiled at as you looked down at the gifts. “What’s the occasion?”

One of his painted eyebrows lifted in surprise then he looked down at the flowers and chocolate before shrugging. His smile returned as he grabbed your arm and lead you over to the bed. 

“Well now sugar plum, this is a very. Very. Special occasion. I can smell it on you. Your fertile little womb is ready. Time to breed you up girl.”

The smile fell from your face.

Pennywise pulled his gifts from your hands and pushed you back on the bed.

“Breed? Papa, what.. what are you talking about?”

The clown, or whatever he really was, sensed your discomfort and frowned. A low growl echoed in his voice as the act slipped for just a moment. 

“Breed. As in YOU are going to birth my offspring. What the hell did you think you signed up for when you agreed to be my mate?”

You crawled higher on the bed when you noticed the writhing bulge moving around in his clown costume.

“I thought.. what we have been doing was..”

He snorted, then smiled and threw his head back as he laughed. 

“You thought that was it? HA!”

He turned back to face you with inhuman yellow and red eyes and grabbed your ankle with bruising force.

“That was just a little bit of fun. Practice. I had to make sure you could take Papa's cock well enough before the real show began. Now...” 

He pulled you down the bed, his form shimmered with barely contained need.

“Spread your legs and let’s make a fucking baby”


	6. Chapter 6

**Notes for the Chapter:**

> "Help me set this fucking thing on fire"

With a final scream and push, you delivered your first child into the waiting arms of the father. 

“Papa.. hows the baby? Is he alright?”

The old clown hummed as he wiped the baby off and stood beside the bed. He examined the baby with his odd, silver eyes and smiled. 

“He’s…Ugly.”

Your face fell and you pulled yourself up against the headboard.

“What?”

“I say we get rid of this one and try again. Whaddya say honey-bun?” He handed the bundle over to you and waved his hand, igniting his thumb like he did when he lit a cigar. 

“Help me set this fucking thing on fire and I can put another one in ya?”

You screamed, and cradled the bundle to your breast in an effort to protect it as Papa’s wide smile stretched across his face. His eyes crinkled in the corners while you stared at him and suddenly he was laughing so hard he could hardly breathe. He shook his head, sending his soft crown of red hair waving back and forth as his mouth hung open in an odd barking laugh.

“Thats.. not funny Papa..” 

The first stages of shock were passing and tears blurred your vision.

“Aww.. babydoll. Papa was just funin! I've waited for this day a long… L O N G time. The boys got killer looks too! Takes after his Pop.”

He smiled at you and elbowed you in the ribs until you slowly started to smile back.

“You know I have ta.. clown around!” His mouth stayed open in a grin as he reached up and honked his nose twice. In your arms, the bundle giggled.


	7. Chapter 7

**Notes for the Chapter:**

> "All fours. Now."

“All fours. Now.” 

You sat bare before the old clown, clad only in your stockings and your new collar. You nodded, and crawled into position at his command. 

“That’s a girl.”

Papa smiled as he stepped up to the side of the bed and stood in front of your. He leaned over your body and grabbed your hips to move you into the position he wanted. Your face flushed as you realized what he was doing. He chuckled as he lined you up with the full length mirror. Now he could watch your cunt drip while he used your mouth.

His attention returned to you and he stroked your cheek with a gloved finger.

“Who do you belong to, kitten?”

“You, Papa.” 

His smile widened as he tapped your nose with a finger.

“That’s right sugarplum. Now, make Papa happy.”

He reached into his costume and pulled out his heavy cock before pressing it against your lips.

Pennywise’s cock was almost close enough to be considered human. He had taken many forms with you but this was by far his favorite. It was long and thick. As white as his face, with a slightly pointed head that was as red as his nose. In the center of his cock, his width expanded even more into what could only be best described as a red knot.

He pressed against your mouth and you eagerly took him down. His knot brushed against your lips and you swiped out your tongue to lick underneath it before hollowing out your cheeks and sucking back up his member. 

“Ohhh baby.. that’s it. Just how Papa likes it.”

He allowing you to bob on him at your own leisurely pace while he reached down to grope your tits. With a groan, his other hand slid down the arch of your back, further than he should have been able to reach, and squeezed your ass. “You got a great body doll.”

He spread your cheeks, giving himself a nice view of your holes before his fingers dipped into your pussy.

"So wet and ready for me."

He pumped his fingers in and out, then slid them up to your ass. Papa swirled your own lubrication around your hole before pushing his middle finger in.

You arched your back for him a little more and started working your lips around his knot. Thick strands of your saliva mixed with Papa’s natural slick, helping you take more and more of him. 

“A body like this.. makes me wish there were more of me.”

Glass shattered behind you but Papa grabbed you by the hair and kept you in place. 

“Just relax princess, this is gonna feel reallll good.”

You melted under his touch and focused on the task at hand even when you felt a second set of gloved hands squeeze the globes of your ass.

The Papa in front of you continued to hold still while you pushed your mouth down and around his knot. It was painful getting over it but once he was in, his knot pushed against the back of your teeth, locking him in place and making sure you could only move forward

You felt another pointed tip rub between the slick folds of your cunt before moving up to press against your tight ring of muscles. Deceptively strong hands held you wide open as he slowly slid it. 

“Thatta girl”

The Papa in front of you praised you as his hand returned to your breasts. The cock behind you pushed in until the knot was pressed tight against your ass. You braced yourself and closed your eyes as the pressure built and built until finally, he entered you with a pop. You moaned around the cock in your mouth and Papa shivered. 

“Good girl. You love taking Papa’s knot, dont'cha? Don't matter what hole.”

Weight settled against your ass as the Papa behind you entered you fully. He grabbed your hips in a firm hold and started roughly thrusting into you, forcing you down further on the Papa in front. Your eyes rolled as you felt his knot pulling at your insides, his heavy balls slapped against your clit even as you licked at his thick base.

This was bliss


	8. Chapter 8

**Notes for the Chapter:**

> "Whats the matter? Can't keep up?"

Your arms were too weak to push him away, but the clown held you down while he thrust into your body anyway anyway. 

“Papa.. please.”

Pennywise finished with a grunt and pulled out of you. Fresh cum leaked from your swollen and bruised pussy before soaking into the stained mattress. He watched it, then chuckled as he moved from the bed and lifted a bottle of clean water up to your lips. 

“Drink up. Can’t have my little toy dying from dehydration, now can I? It’s not as fun when you go all... cold and silent.”

Papa threw his head back and laughed but the humor was lost on you.

You finished drinking and he let your limp body fall back on the dirty mattress. Papa resumed his position between your legs and stroked his thick cock back to life. 

“Be a good girl and open up for me.”

You shook your head and tried to close your legs.

“No.. please Papa. I need a break.”

He slapped on an overexagerated pout and he leaned over your body. 

“Aww.. what's a madder, sugartits? Can’t keep up with this OLD clown?”

Again, you shook your head no and looked up at him. Tears pricked the corner of your eyes as he laid the bulk of his body down on top of you, balancing his cheek in the palm of his hand.

“Dont'cha have something to say?”

His painted eyebrows raised as he waited and you licked over your dry lips. 

“I’m s..sorry I called you old.”

Papa’s eyes flicked to the side before turning back to you. He tilted his head.

“Annndd…?”

“And I’m sorry I said you finished too fast.”

The clown laughed in your face and grabbed your nose.

“Make no mistake babydoll, I use you for exactly as long as I want to. Now, spread those legs for Papa. I’m not finished with you yet.”


	9. Chapter 9

**Notes for the Chapter:**

> "Stop being so attractive!"

A low whistle caused you to jump and you turned to look over your shoulder at the red haired clown standing behind you. Your hand covered your racing heart and you flashed him a nervous smile.

“Papa..you scared me!”

He had caught you bending over and his eyes remained glued to your panty clad ass.

“I ever tell you that you got a great ass, sweet cheeks?” 

He smiled wide and swung his arms as he strut over to stand directly behind you. Your face flushed from his close proximity and you turned away from him.

“Once or twice.”

“Mmmhmm..”

Pennywise bent down and ran his gloved fingers up the back of your thigh before grabbing a handful of your ass. Red lips ghosted over your shoulder as he squeezed, hard.

“Well sugar, you’ve got a great ass.”

He slapped it, making your cheeks jiggle, then pressed the bulge in his costume tight against your ass. Hot breath hit the back of your neck as his fingers trailed around the top of your thigh, then brushed over the front of your panties.

“Bendin’ over and teasing an old man like that… and here I thought you were a good girl.”

“I am.”

You ground your ass up and down against his bulge and leaned your head back to rest on his shoulder. His free hand worked it’s way under your shirt and he palmed your breast before rolling your nipple between his fingers.

“Prove it. Hold still and let Papa use those thighs of yours.”

Quickly you nodded and held still as you heard the sound of fabric ripping free. His thick, hot cock slid between your thighs and rubbed against your already wet panties. 

“That’s it babydoll. Good girl.”

One clawed hand held your hip as he bent you over and started to grind against your cunt. 

“Mm.. Papa.. are you ever going to get your fill of me?”

You turned to look back at him and ran your tongue over swollen lips. He squeezed your breast hard enough to bruise and you whimpered.

“Maybe when you stop being so attractive.”

He laughed and you wondered what was so funny.


	10. Chapter 10

**Notes for the Chapter:**

> “I’m gonna fuck you so hard that you forget you ever even met that asshole.”

She didn’t seem to notice him sitting in the recliner as she came in and slammed the front door. She didn’t notice him at all until he exhaled a thick cloud of cigar smoke and spoke to her. 

“What'sa matter princess? What has my girl so upset, hmm?”

She jumped and turned to face him. Her eyes were puffy, and red rimmed. Of course he knew what was bothering her, but he wanted to hear it from her.

“Papa?”

Her face crumpled and she sobbed.

“Oh now.. come on over here and tell Papa allll about it.” 

He flicked the cigar off into the darkness and pat his lap. Like a loyal dog, she obeyed.

She tucked her face into the ruffles of his costume and he stroked her back as she told him the story. Her ex had caused a scene and embarrassed her at work. He knew that of course.. he saw everything that happened in his town and he would deal with the matter later. It's not that he cared about her feelings.. oh no. But she was HIS.

He rubbed her skin and whispered soothing words to her and eventually her sobs turned into quiet sniffles. 

“There now. There we go. That’s my girl. You trust Papa to make it all better?”

She nodded against his costume and looked up at him with adoring eyes. An amused smile lifted the corner of his lips as he started to run his gloved fingers up and down her bare thighs, playing her body like only he knew how.

She moaned, and leaned back for him. Her legs spreading a little as the tips of his claws poked through the silky gloves. Her breathing was uneven, her eyes hooded with lust as he moved his hand up her skirt to her panties. He was pleased to find she was already wet for him.

“Look at that princess, your panties are all wet for Papa… naughty girl. Let’s get you out of these wet clothes and then I’m going to fuck you so hard that you forget you ever even met that asshole. Does that sound like a plan, baby doll?” He smiled wider at her and she wiped her eyes before nodding again.

“Yes Papa. Please”


	11. Chapter 11

**Notes for the Chapter:**

> "Your ass is gonna be seven different shades of red after that little stunt.” 

“Bet'cha thought that was reeaaall funny, didn’t you?”

The gravely voice belonged to the old clown who stood behind you, just out of your field of vision.

“Well, I did. Until now.” 

The sharp crack of a leather belt snapping together caused you to jump and your smug smile fell off your face.

It had been a simple prank, more of a joke really, but it seemed like the humor had been lost on Papa. In a matter of moments you had found yourself in your current predicament; back in your bedroom, stripped completely naked, and bent over your bed with your hands tied to your headboard. Any hope that Papa was just going to fuck an apology out of you quickly went out the window as you felt the heavy leather strap run up the back of one thigh, across your exposed ass, and down the back of the other.

“You really want to have a smart mouth with me little girl? Your ass is going to be seven different shades of red after that little stunt, and then we’ll see who’s laughing.”

You heard the crack of the leather seconds before you felt the hot kiss across the flesh of your ass. You screamed and squirmed against your bonds, trying to find a way to cover your rear from the brutal assault.

Another crack and another blow, this one to your other cheek. Hot tears ran down your face as pain bloomed like the bruises sure to follow.

“Hold still girly. Wouldn’t want me to miss now would ya?” 

Papa’s voice carried a hint of amusement and you sobbed as you forced your legs to steady. You held your ass out for him.

“Thatta girl.”

The next blow caught you on the bottom of the cheek and licked across the top of your thigh. You cried out and flinched, but quickly recovered.

Four, five and six were taken in stride. Papa was hitting a different strip of flesh with each blow and it seemed a little easier when you could guess where the next one would land. Still, you cried out with each strike and by the time he was on seven your face was a dripping mess.

Where was seven going to land?

“Spread ‘em a little wider for Papa.”

You shook your head in disbelief. 

“Please Papa no… not there. I’m sorry. I..”

The leather belt snapped together again and you involuntarily clenched your legs together.

“There will be plenty of time for your apologies when I’m finished. Now, spread your FUCKING legs or I’m going to start all over!”

Your whole body trembled as you obeyed.

The last crack of the belt whipped across the apex of your thighs, catching your clit in the process. You screamed as your legs finally gave way and you collapsed on the bed, crying and rocking your hips while you tried to soothe the burn.

“There there sweet cheeks. That wasn’t so bad, now was it?” 

Papa’s soothing voice sounded next to you as his familiar weight sank onto the bed. His gloved hand rubbed over your bruised and bleeding flesh before he cupped your sex. The pressure alone helped to ease some of the sting.

“What do you have to say for yourself now princess?”

“Im.. I’m sorry P.. Papa..”

The bonds around your wrist dissapeared and Papa brushed the hair back from your sweaty face.

“Annndd??”

“And I’ll.. never do it again. I promise.”

“Good girl.”


	12. Chapter 12

**Notes for the Chapter:**

> "I'll keep you warm."

It was snowing like crazy and you felt the chill all the way to your bones. All day you had felt like you were freezing and no amount of blankets or soup seemed to help the cold ache inside.

The temperature continued to drop as night fell and not even a hot shower warmed you up. Your hair was still steaming while you hurried to dress in your thickest pajamas then crawled underneath your pile of blankets.

“Ss….so cold…” 

Curling in on yourself, your teeth chattered and you shivered. As the laid there, you felt it. The slight change in pressure as what was previously empty space was suddenly filled. A familiar weight settled in under the blankets behind you.

“I can hear your teeth chatterin’ from all the way down in the sewers babydolll. You need Papa to… warm you up?”

Warm breath hit the back of your neck and your senses were filled with the presence of the old clown.

Pennywise wrapped his arm around your waist and pulled you back until you were tucked tight against his bulk. A quiet moan slipped passed your lips and you leaned into his warmth. 

“Papa… you’re warm.”

He chuckled and pressed his painted lips against your neck. His hand ran underneath your shirt and up to squeeze your breasts. 

“I told ya kiddo, I can be anything.”

He palmed your breasts and rubbed them in a circular motion before he tweaked your nipples then flicked them with his fingers. Your eyes snapped open as you realized it was skin you felt against you, not fabric.

“Skin to skin works best for warming you up, dont'cha think?”

Papa wrapped his arm underneath your body and continued to lazily play with your tits. His other hand slid down your side and dipped into the front of your pajama pants.

“See? Look at that. Already heating up for ol Papa aren’t you?”

You nodded, and sucked in a breath as his fingers brushed against your clit then expertly prodded at your slick hole. You moaned and pushed your hips back against the bulge you felt poking at you from behind. Papa slid his fingers inside.

“P.. Papa.. that feels so fucking good!” 

He twisted your nipple, making you cry out in pain while he continued to finger you.

“Better watch that filthy mouth of yours girly.”

Pennywise pulled his fingers from inside you and yanked your pajama bottoms down to your thighs. A firm hand gripped your hip and held you still as the pointed tip of Papa’s cock slipped between your thighs. He pulled you back while he thrust forward and you moaned even louder when the thick knot in the middle of his cock rubbed against your wet pussy.

He used your thighs, thrusting at a slow pace while you whined and squirmed against him almost desperate for him to put it in. Finally, he laughed and lifted your leg only as much as the pajama pants around your thighs would allow. 

“Needy little cunt.”

Papa’s tip pressed against you and he slid in up to his knot. He thrust like that, halfway in, just enough to tease you until finally, with a groan his grip on you tightened. He pushed his knot deep inside, locking him in place.

Your muscles clenched down around him and he lowered your leg back down. His fingers went back to your clit where he rubbed it in tight circles while he continued his slow, leisurely pace. The arm underneath your body never let up on your breasts and soon you were panting for air. A thin sheen of sweat coated your skin as you rut back against him, desperate for release.

“Please Papa.. I’m right there.. please let me cum!”

He laughed at your pathetic whine.

“Already?… alright girl. Cum on Papa’s cock.”

The angle of his thrusts changed. He was pushing deeper. The knot in his cock rubbed right against your sweet spot and you screamed as you came around him. A few more deep thrusts and Papa grunted behind you. His cock pulsed and you felt his hot cum pump deep into your pussy.

“Nice and warm in here. I think I’ll stay all night.” 

His heavy arm rested around your middle and you wiggled your hips, still feeling him inside you.

“Quit that moving girl and go to sleep. I’ll keep you warm.”


	13. Chapter 13

**Notes for the Chapter:**

> "Saddle up, doll."

It had been a very long day and you had some… tension built up.

You contemplated breaking your rules and spending some 'quality' time with yourself, but no sooner had you stepped through the front door when the scent of cigar smoke hit you.

“Hullo there sweet cheeks.” 

The gravely voice of the old clown welcomed you and you smiled as you walked into your living room. Papa was guaranteed to leave you feeling satisfied. But sometimes he required a little.. coaxing.

“Hello Papa.” 

Your heels clacked across the hardwood as you went to him and kissed his cheek.

“How was your day today? Anything new and exciting happen?.”

A crooked smile slid across his painted lips and his eyes dropped to your ass while you went to fix him a drink. He took a long pull of his cigar before he answered.

“Same ole same ole, kiddo.”

The subject of your small talk never mattered to Pennywise. You could tell him you had went on a murder spree and he wouldn’t have bat an eye. No, Papa got a kick out of playing with you and he lived for that domestic shit.

Like the ever obedient toy, you fetched him his glass of amber liquid and he accepted it gratefully before reclining back in his chair.

“You know Papa, I had a long day today.”

You stepped away from him and unzipped your dress. It fell to the floor, leaving you in nothing but your underwear and heels.

You had his attention now.

His eyes leisurely traveled over your body while he puffed on his cigar. He set in to the side and pat his lap as he exhaled. 

“Why don't you come sit on Papa’s lap and tell me all about it.”

A sweet smile of your own graced your lips as you turned around and planted your ass firmly against the crotch of his costume. Underneath you, his body stiffened in surprise. He had been expecting you to climb into his lap like usual.

“It was just.. one of those days today. You know what I mean Papa?” 

You made it a point to wiggle your hips when you leaned over to take off your heels. A gloved finger ran down the arch of your spine and you moved your hair out of the way so you could look back at him from over your shoulder. You shrugged and put on that fake innocent expression that drove him wild. It was a fun game between you two.

“I just feel like I’m empty.. like I’m missing something.. inside. Do you know what I’m trying to say, Papa?”

Pennywise laughed and set his drink down. 

“Oh, I know exactly what you’re looking for princess and have I got good news for you.”

He suddenly leaned forward and grabbed you around the waist. His vice like grip guided your motions, making you grind down on his crotch.

“Saddle up, doll. Papa wants a ride”


	14. Chapter 14

**Notes for the Chapter:**

> "The only way you're getting off is on my thigh."

“That’s it girly..swallow it all down.”

Pennywise held your mouth down on his thick cock as he twitched, once, twice and then shot his hot load down the back of your throat. You closed your eyes as you fought the urge to gag and swallowed until Papa’s grip on your head relaxed. He groaned, satisfied with your performance. 

“Good girl.”

He pat you on the head and you were finally allowed to pull back from him. Your jaw hurt, and opening it wider to pass over his knot brought tears to your eyes. 

“Thank you Papa.”

You worked your jaw side to side before looking up at him and leaned forward to lick his tip clean.The monstrous appendage jerked against your tongue and Papa glared down at you.

A cigar appeared with a flick of his wrist and the tip ignited. He took a deep drag then blew smoke down into your face.

“You wouldn’t be trying to get ol Papa worked up again, would you babydoll?”

You held your hands down against your thighs. There was no point in lying to him anyway. He could see.

“Because you know the rules. What are they?”

You tried to look down but a clawed finger looped under your red collar and pulled, forcing you to look up into his yellow eyes. 

“I asked you a question girl.”

“Bad girls don’t get cock for a week.”

A smile spread across his painted lips.

“That’s right. And by my count you have two more days to go. Although…” 

His eyes returned to normal as he looked over your nude body.

“You were very good just now. Tell ya what kiddo.”

Pennywise sat up straight and pat his hand on his thigh.

“I’ll let ya grind one out as long as you make it fast.”

You stared up at him with wide eyes before looking back down to the cock you craved so much.

“But.. Papa. Please.. I.”

He growled low and grabbed you by the chin. “The only way you’re getting off is on my thigh. Take it or leave it. Doll.” 

His smile returned and he shrugged before leaning back in his chair. Another drag of his cigar, another smokey cloud.

“Hurry up. Before I change my mind.”

Quickly, you stood up and straddled his thigh. Desperate for release, the thought of being denied your only chance for an orgasm wiped away any protest you might have made.

“Hold your arms together behind your back. I want to see them tits jiggle. Don’t fall now.” 

His smile was cruel but you obeyed and held your elbows behind your back.

“Yes Papa.”

You lowered down on his thigh and sighed as the silky material of his costume brushed against your pussy. The muscles hidden below the deceptively bulky costume finally gave you the friction you needed and you moaned. 

You started slow at first, rocking your hips back and forth, grinding down against your clit whild you rubbed up and down his thigh. Soon, you were building speed, panting as you chased your orgasm.

“I can feel that wet little cunt soaking through my costume. Nasty little slut. Desperate fucking thing.” Pennywise watched you and smoked his cigar as you came undone against him and screamed his name.

Maybe if you put on a show, he wouldn't make you stop.


	15. Chapter 15

**Notes for the Chapter:**

> "Someone's gonna hear you."

It was that time of year again, your company Christmas party, and everyone was drinking and having a good time. Of course, you had realized early on that more than a few of your coworkers were trying to get you underneath the mistletoe. While you were flattered, frankly, you weren’t interested. Not anymore.

Someone called out that another bottle of wine was needed, and you jumped at the opportunity to distance yourself from the jolly crowd even if it was only for a moment. The wine was being kept chilled in the break room and you hummed ‘joy to the world’ as your heels clacked across the tile to the refrigerator. Bending over to reach another bottle, your nose wrinkled when you caught an off putting scent. It smelled like someone had forgotten to throw away their lunch.. something smelled almost.. septic.

“Well.. Merry Christmas to me.”

The rough voice came from behind you and you gasped as you turned around. The wine slipped out of your hand but gloved fingers snatched the bottle out of the air before it could smash against the tile. The old clown was dressed in a dingy Santa costume instead of his usual fare, and he titled the bottle up to study the lable. 

“Not bad. Although personally, I prefer something a little more... full bodied.”

A crooked smile stretched across his lips as he leaned closer, pinning you against the counter while he set the bottle down.

“Papa. What are you doing here?” 

Pennywise had first appeared to you at the beginning of fall and had since become your unlikely lover of sorts. Still, he scared the hell out of you.

He raised his eyebrows and held his hand over his chest in mock hurt. 

“Me? Why, I just came to see my girl before I go out hunting for the night. And what a sight there is to see.”

You knew exactly what he meant by hunting and you shivered when he looked you up and down. Your hair and makeup were flawless. Your cheeks were tinted pink from the alcohol and the red dress you wore was appropriate, but flattering. The flared skirt was decorated with prancing reindeer silhouettes. Black heels finished the look and Papa nodded approvingly.

“I got a little itch I need to scratch doll.”

Pennywise dropped his tone as he stepped closer and pressed your body back against the cabinets. Without hesitation, you tilted your head to the side for him. His hands gripped your waist and the tip of his tongue pushed past his thin lips, trailing over the pulse in your neck.

“And you know the rules.”

His breath was hot against your skin and you closed your eyes before nodding.

“Whenever and wherever.”

“That’s right sugar plum.”

His hand slid up your side and squeezed your breast, causing you to moan. Anticipation and arousal flooded your body as you prepared to satisfy his needs.

“Ah ah!”

He pulled back and waved a finger in front of your face.

“Someone’s gonna hear you if you keep moanin' like a whore.”

The finger tapped the tip of your nose before pushing past your lipstick smile and into your mouth. There was no time to react or to make a sound of protest as the clown started to pull a long stream of colorful scarves from your throat. The cloth tickled the back of your tongue. On and on it came until finally, Pennywise pulled and your body moved with it.

He guided you to the middle of the tile floor and wrapped the scarves around your head, looping them over and over until you were properly gagged. Silent night started to echo down the hallway and he chuckled as he spun you around and bent you over.

“Couldn’t have planned that better myself.”

Papa kept a tight grip on your hair to keep you from falling face first as he lifted up your skirt and ran a finger over your damp panties. 

“Gotta make this fast babydoll. Wouldn’t want them to come looking for you, now would we?”

He slapped you on the ass and you spread your legs wider for him. Fabric rustled as he pulled your panties to the side and you felt his thick cock press against you. The pointed tip prodded your hole and then he was pushing in, deeper and deeper, past his knot until he sat fully sheathed inside you. He groaned, you whimpered.

Pennywise grabbed your elbows with both hands and used them for leverage while he started to thrust. Your heels slipped, and your face dipped dangerously close to the floor, but Papa effortlessly kept you standing. 

“Feels fucking good, don’t it?

You moaned as he used your body. He thrust harder, faster. Quickly pushing you closer to orgasm.

“Take it all. Take Papa’s fat cock like a good little Santa slut.”

Amusement mixed with the animalistic desire in Papa’s voice and you realized just how much he was enjoying this. You could still hear the party going on down the hallway and your heart raced as you wondered just how long until one of your co workers came to find you. How long until they looked in the breakroom? What would they see when they did? The risk of getting caught was too much. With a muffled cry, you came around Papa Santa, squeezing and milking his inhuman cock while he held you upright.

“That’s it.. that’s it!”

He snarled behind you. The bruising grip on your arms tightened as his cock throbbed, filling your insides with his hot cum. He didn’t wait for you to recover before he pulled out of your overly sensitive cunt. You winced as his knot cleared your opening and you heard his cum splash down on the tile.

“Looks like a white Christmas to me.”

He laughed his strange, barking laugh as he fixed your panties and pat you twice on your bottom. The scarves dissapeared from your head and you gasped as you tried to catch your breath.

“Better fix yourself up doll, I hear ‘em comin for you.”

He placed his hand under his chin and wiggled his fingers before fading away.

“Shit!” 

You straightened your skirt and grabbed some of the holiday napkins, desperate to clean the cum off the floor. You could feel it soaking into your panties, but there was no time to clean yourself. You shoved the soiled napkins into the trash can just as your coworker came through the doorway.

“There you are. We’ve been waiting on you to come back.” 

His smile was smug as he leaned against the wall. He had been trying to kiss you more than any other man that night.

“Sorry.” 

You smiled apologetically as you held up the cold bottle of wine.

“Couldn’t find the corkscrew.”

You knew full well it was in the other room. It was a feeble excuse, but he shook his head and smiled as he put his arm around your shoulders.

Suddenly, he flinched. His eyes went wide and he pulled away from you like your body had burned him. Some animal part of his brain was screaming, telling him that touching you was dangerous.

He cleared his throat and tried to play it off. 

“Its.. uh.. right in here. Come on, I need another drink.”

He walked in front of you and didn't try to touch you again.


	16. Chapter 16

**Notes for the Chapter:**

> "Come sit on my lap."

The chair rocked as you tried to move your hips, but his grip was deceptively strong. Gloved hands held you down over his face and you moaned. The noise was muffled by the thick cock filling your throat. It wasn’t often that Papa was in such a giving mood and your eyes rolled back as his long tongue lapped at your clit.

“Feelin’ good kiddo?” 

His voice was huskier than usual and he chuckled as you twitched. The feel of his hot breath against your skin was almost too much. Thick arms wrapped around your thighs and his fingers probed at your holes. The feel of them pushing inside you really was too much, and you released his cock with a wet pop.

“Papa!” 

You panted and laid your face against his thigh while you continued to stroke his cock with your hand. You rubbed him, squeezing the knot just the way you knew he liked it and he groaned in pleasure.

“What is it babydoll? You better have a good damn reason for spitting it out.”

“Please.. I want to feel you inside.” 

Hoping to please him, you leaned forward and sucked on the red pointed tip. His cock bobbed as he laughed.

“So, you wanna cum on Papa’s cock, do ya? Filthy slut. My tongues not enough for your needy little cunt?”

He moved his hand and you yelped as he slapped your pussy.

“No! That’s not it.”

You whimpered and gripped the thighs of his costume.

“I just want to feel it inside. It feels so good inside.”

You hated the desperate whine in your voice but you would do anything… ANYTHING to feel him.

“Well, can’t say no to my pet when she asks like that now can I?” 

He could, you both knew it, but he was in a very giving mood and pat his lap.

“Come sit on my lap. Bounce on my cock. If you want it you’re going to do the work.”

You felt like the luckiest girl in the world as you rushed to obey.


	17. Chapter 17

**Notes for the Chapter:**

> "Bite me."

“Faster!” 

Amusement saturated the deep voice behind you.

“I’m going as fast as I can Papa.” 

Your hands were braced on the foot rest of the old clowns recliner. Said clown was seated in said chair.

“Come on girlie, you can do better than that.” 

His gloved hand slapped you on the bare ass almost knocking you off balance.

“Put your back into it.”

Your head hung in shame and quiet resignation as you arched your back and started popping your hips faster.

“Thatta girl.” 

Pennywise laughed. His hot breath hit the wet flesh of your pussy as you fucked yourself on the uncut cigar in his hand

“Ya know, when I told you to do this I half expected you to turn me down. But you just can’t resist ol Papa, can you?” 

His hand rubbed over your ass and squeezed.

“You’re a desperate little whore, ain’t cha?”

He slapped you again and laughed as you stumbled.

“Bite me.” 

The words were out of your mouth before you could stop them and you froze. His laughter continued even as his arm wrapped around your hips, locking you in place with a vice like grip.

“Don’t mind if I do”


	18. Chapter 18

**Notes for the Chapter:**

> "I'm not going to touch you unless you beg."

“You need to get off your high horse princess. Get taken down a peg or two.”

Pennywise, took a deep drag of his cigar before pointing it at the nude woman standing in front of him. One eye squinted as he exhaled. His lip curled in a sneer.

“I’m not touching you again unless you beg for it.”

“Beg for it?”

She scoffed and crossed her arms over her breasts.

“You heard me sugar tits. Your heads gotten too big. You think you run shit around here, but you don’t run anything. Hot pieces like you are a dime a dozen. But me? Well, there’s only one me.”

She turned to glare at him, a defiant look on her face.

“I’m not begging some old man to fuck me!”

Anger flashed across his face and he snarled as he took a step forward. She flinched, bracing herself for his anger, but he stopped short of her and .. laughed. Red and yellow eyes slowly looked her up and down, his laugh faded.

“Have it your way.”

He turned around before disappearing from the room.

***

Months passed and she was growing desperate for release. The old clown cut her off at every attempt, mocking her, telling her to give in, to beg for it and let Papa take care of her but stubborn pride kept her going.

Finally, she couldnt take it anymore and grit her teeth.

“Papa. Please.”

The air around her seemed to pull taut and she had the sudden feeling of falling as the room spun. She stumbled and hit the ground, scraping her palm on the cold concrete floor of the cistern.

“What was that?”

Her eyes snapped towards the sound of the voice and there he was. The subject of her desire and torture. He sat in his chair like he didn’t have a care in the world and watched as she pushed herself off the ground and tried to wipe the grime off her body.

“I asked you a question girl.”

She glared at him and tucked a loose strand of hair behind her ear before she straightened.

“I said please.”

The old clown tapped a finger against his lips and considered her words.

“No. That’s not good enough. Try again.”

“Not good enough? NOT GOOD ENOUGH! That’s what you wanted to hear isnt it?”

Pennywise sat up in his chair and growled.

“The right words dont mean shit if you haven’t fixed your attitude.”

Her hands closed into fists as she took a step towards him.

“Of course I have an attitude! Nobody in this damn town will even look my way. Hell, I can’t even touch myself because YOU wont allow it! I did what you asked and..”

Pennywise jumped up from his chair and crossed the room, grabbing her by the jaw.

“And I will keep it that was for as long as I want. I am a god and you? You are nothing!”

He raised his hand and pressed his middle finger and thumb together to send her back to her room like an unruly child.

“Maybe another few months without being touched will change your tune.”

“No!”

She slipped from his grasp, dropping to her knees as she finally broke.

“Please Papa Please… I can’t take it anymore.”

She sobbed. Tears started to run down her cheeks, smearing her makeup.

“I.. need you.”

His laugh made her look up at him and he smiled as he stroked her hair.

“There. That wasn’t so hard now was it?”


	19. Chapter 19

**Notes for the Chapter:**

> “If you interrupt me one more time, so help me god!”

The old bastard had a wicked sense of humor. One that you didn’t share.

His newest form of amusement was scaring the shit out of you anytime you decided to spend some alone time on some self love. It never failed, right before the moment of sweet release, Pennywise would pop out of nowhere and ruin the moment. Sometimes it was with one of his lame jokes. Sometimes he wore the appearance of a horrifying monster. Once, it was an air horn.

And oh, how he loved it! He would laugh until he couldn’t breathe. The red mop of his hair bouncing as he doubled over and slapped his knee. To say it was getting on your nerves would be an understatement.

You lay flat on your back, one hand underneath your thin tank top teasing your nipples while the other furiously rubbed your clit. Your eyes were closed in concentration. You had to hurry. It felt like if you didn’t cum this time you might actually go insane.

“F… fuck..”

Your mouth hung open as you felt it build. So close.. almost… 

Something tickled your face and you opened your eyes. A balloon floated directly above you. The dangling string brushed against your face.

“What the..”

The balloon popped, causing you to scream as rainbow confetti rained down on you.

“God damn it Pennywise! If you interrupt me one more time, so help me god!”

“I don’t think he’s gonna help you, princess.”

The clowns gruff voice made you jump and you turned to find him stretched out on the bed beside you. His head was propped up on his hand. Painted eyebrows raised in amusement.

“Oh, fuck you Papa!”

You froze as soon as you said the words but the clown only laughed. His hand closed around your wrist and with deceptively inhuman strength, he pulled you until you were straddling his hips.

“Hey now.. there's an idea.”


	20. Chapter 20

**Notes for the Chapter:**

> “feel how much I want–need–you”

Uncomfortable.

The day was uncomfortably hot. Your clothes clung to your sweat soaked body.

Sensitive

Every movement drug the material of your clothes over your sensitive flesh. Your nipples were hard pebbles inside your bra, your panties soaked through with arousal.

Desperate

You leaned back in your chair and fanned yourself with your magazine. Desperate for relief, you picked out an ice cube from your lemonade and ran it over your collar bone. Closing your eyes, you moaned from the cool sensation.

“That’s a sound I like to hear.” 

Your eyes snapped open at the sound of the gruff, familiar voice.

He was sitting on the railing of the porch staring at you, a smirk twisting his lips. Despite the heat, he seemed perfectly at ease in his clown costume. Not even a drop of sweat spotted his painted brow. Not that you had really expected it to.

“Pennywise.”

“The one and only.”

He watched as a drop of water ran down your chest and dissapear in your cleavage.

“So, you can feel it.”

“Feel what papa?”

There were children playing across the street. People walked hand in hand down the sidewalk and you wondered how they could wear jeans and light jackets in this heat! If your air conditioner hadn’t been broken, you wouldn’t have even dared to be outside.

The old clown smiled at the nickname.

“You can feel it in the air. Feel how much I need you.”

His expression changed along with his eye color and suddenly, you were reminded that he was the predator and you were the prey. Your legs wobbled as you stood up from your chair and started to back into your house. There it was again. Uncomfortable. Sensitive…. desperate. Heat.

“Papa has needs babydoll.”

He slid from your bannister and followed you into the house. The door closed behind him.

“And you’re gonna help me.”

**Notes for the Chapter:**

> This completes my drabble collection until I open requests on tumblr again.


	21. Chapter 21

**Summary for the Chapter:**

> "Daddy's home from work, pet. Have you done everything I ordered you to?"

“Daddy’s home from work, pet. Have you done everything I ordered you to?”

You spun around and pressed your back against the sink. You hadn’t heard the older clown come in, but then again, he probably hadn’t used the door.

“Papa, you startled me.”

He smiled at you but it didn’t quite reach his eyes. The warning was there.

“I asked you a question girlie.”

You pushed away from the sink and dried your hands on your apron before folding them in front of you while you recited your chores. That seemed to please him and his grin spread wider.

“Well, you’ve been a busy little bee today. You must have busted your ass to get all that done.”

He chuckled in his deep, smokey way and took a step closer. His eyes dropped down to your skirt.

“And what about the rest of it? Did'ya follow my orders?”

Heat rose to your face as you dropped your eyes in embarrassment, and nodded.

“Yes Papa.”

“Don’t mind if I check for myself do ya?”

One of the kitchen chairs pulled back from the table on it’s own and Pennywise flopped down in it. He braced one hand on his knee and beckoned you with the other. It wasn’t a request.

“Bring your ass over here.”

You didn’t bother taking off your apron before you rushed to stand in front of him. He shoved his hand up your skirt and you gasped as his warm glove covered your bare mound.

“No panties? Good girl. Now bend over so I can check the other place.”

He grabbed your hips and spun you around until you were bent over the kitchen table, then lifted your skirt up around your hips. You felt his hands on your ass, kneading, squeezing, before he spread your cheeks open and laughed. His hot breath hit your skin and you bit your lip to keep from squirming. It was beyond embarrassing.

“You been wearing this all day?”

You nodded again as you felt him poke at the pink jewel of the butt plug. He tugged on it, but your body wouldn’t let go.

“That’s my girl.”

He twisted it inside you, then slapped you hard on the ass.

“You’ve been such a good pet. I think you deserve a little treat. Whadda ya say?”

He didn’t wait for an answer before he spun you back around and grabbed your legs. In one quick motion, you found yourself on your back, spread out on the kitchen table. Dishes shattered as the dinner you had worked so hard to prepare clattered to the floor. Papa already had his thick cock in his hand as he stepped on the chair and climbed up on the table between your legs.

“Don’t worry princess, you can eat off the floor when I’m done with you.”

He lined up and pushed into your cunt, stretching you, filling you to the line that ran between pleasure and pain while you clung to his shoulders.

“Then after you clean up this mess, I’m gonna pull out that plug for some real fun.”


End file.
